Imidazole → 4-[(tert-Butyldimethylsilyl)oxy]-N-methylaniline

HRID 63659

Reaction equation

HRID 63659 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[CH3:10][C:11]([Si:14](Cl)([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1.O>C(Cl)Cl>[Si:14]([O:9][C:6]1[CH:7]=[CH:8][C:3]([NH:2][CH3:1])=[CH:4][CH:5]=1)([C:11]([CH3:13])([CH3:12])[CH3:10])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 5931n-Methyl-p-aminophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 134173524-[(tert-Butyldimethylsilyl)oxy]-N-methylanilineYield 43.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(methylamino)phenol (5.0 g, 29 mmol), TBDMSCl (4.8 g, 32 mmol) and imidazole (9.9 g, 0.15 mol) in DCM was stirred at r.t. for 1 h. Water was added, and the mixture was extracted with EtOAc. The organic layer was dried (Na2SO4), concentrated and purified by silica gel chromatography (PE:EtOAc=10:1) to give 3.0 g (43%) of the title compound as a dark green oil. [M+H] Calc'd for C13H23NOSi, 238. Found, 238.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography (PE:EtOAc=10:1)

Sources & evidence

ORD record
ord-5dd49465ed79419d95b3eac04ff6c8cb
Source dataset
uspto-grants-2016_09
Patent number
US09447046B2

Linked notes

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